CN105413750A - Preparation method of mimic enzyme - Google Patents

Preparation method of mimic enzyme Download PDF

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Publication number
CN105413750A
CN105413750A CN201510925105.2A CN201510925105A CN105413750A CN 105413750 A CN105413750 A CN 105413750A CN 201510925105 A CN201510925105 A CN 201510925105A CN 105413750 A CN105413750 A CN 105413750A
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nss
preparation
water
alcohol
hemin
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李茂国
耿慧丽
俞木萍
于苗苗
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Anhui Normal University
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
    • B01J31/28—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of the platinum group metals, iron group metals or copper
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/75—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated
    • G01N21/77—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator
    • G01N21/78—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator producing a change of colour
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/84—Metals of the iron group
    • B01J2531/842—Iron

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  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
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  • Inorganic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
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  • General Health & Medical Sciences (AREA)
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Abstract

The invention discloses a preparation method of mimic enzyme. According to the preparation method, firstly, Co3O4-NSs is synthesized from cobaltous acetate tetrahydrate and hexamethylenetetramine with a self-assembly method of a surfactant in a water-alcohol mixture solvent; then, hemin and (Co3O4-NSs) are directly mixed and stirred at the normal temperature, and hemin/Co3O4-NSs two-dimensional nano composite is prepared. Compared with the prior art, the preparation method has the characteristics that the cost of mimetic enzymes of peroxide is low, the catalytic activity is high, the stability is good and the detection range is wide.

Description

A kind of preparation method of analogue enztme
Technical field
The present invention relates to preparation method and the application thereof of analogue enztme, particularly, relate to the preparation method of Mimetic Peroxidase.
Background technology
Native enzyme has selectivity and high efficiency under mild conditions, therefore, in various fields by investigation and application [see ACSAppl.Mater.Interfaces., 2014,6,19207-19216] widely.But native enzyme is deactivation, expensive, purification difficult and consuming time long because of the change of environment easily, brings inconvenience [see Catal.Sci.Technol., 2013,3,2761-2768] to use.Therefore, researcher start to find or prepare not only there is the catalytic performance of native enzyme but also the material of simple and stable to realize the simulation to enzyme function.So develop and both have efficient catalytic activity, the analogue enztme that can overcome again the shortcoming of native enzyme goes to replace native enzyme to be a challenging job.Especially develop Mimetic Peroxidase, it with peroxidase is the same can other material of Catalytic Wet Peroxide Oxidation, particularly to hydrogen peroxide (H 2o 2) there is efficient catalytic action.And peroxidization participates in the pathogenesis of multiple important diseases, biological cell, tissue and even organ damage can be caused.Hydrogen peroxide (H 2o 2) as the important intermediate material of the one in bioprocesses, Accurate Determining is carried out to its content, be significant in analytical chemistry and clinical medicine.
Along with the appearance of nanometer technology, the analogies of the peroxidase based on nano material, the Mimetic Peroxidase especially based on the nano material of lamellar structure has become the ideal of new class and important instrument in colorimetric determination.This kind of Mimetic Peroxidase has advantage more significant than native enzyme, and such as Mimetic Peroxidase has higher stability, low, the easy storage of preparation cost, flexibility etc. in the Nomenclature Composition and Structure of Complexes design.2011, and Guo etc. [see ACSNano., 2011,5,1282 – 1290] prepare the graphene nanometer sheet using Hemin functionalization, this composite has the catalytic activity of peroxidase, can Visual retrieval hydrogen peroxide, and then indirectly for the detection of SNP.But the price of Graphene is costly, which limits the application of this material.2013, and Zhang etc. [see Sen.andAct.B., 2014,192,150 – 156] Hemin is fixed in the intercalation of Fe – Ni double-hydroxide (Fe – NiLDH), prepare Mimetic Peroxidase, and for the quantitative detection of hydrogen peroxide.2014, and Li etc. [see RSCAdv., 2014,4,24256-24262] in order to improve the activity of the class peroxidase of molybdenum bisuphide, Hemin is mixed with the molybdenum bisuphide after ultrasonic stripping, prepare the molybdenum bisuphide composite of Hemin modification as Mimetic Peroxidase.But the range of linearity that above method detects is all very narrow, only only has an order of magnitude, be difficult to meet actual detection needs.
Summary of the invention
Purport of the present invention is just to provide a kind of preparation method with the nano material of high catalytic activity the analogue enztme for the Visual retrieval of hydrogen peroxide in relative broad range
To achieve these goals, the invention provides one based on Hemin/Co 3o 4the preparation method of-NSs two-dimensional nano Simulation of Composite enzyme, described preparation method comprises the following steps:
A) surfactant is joined in water-alcohol solvent, stir 15-60 minute; Add four hydration cobalt acetates and six methine four ammoniums continuation stirring 15-60 minute again; Add alcoholic solvent again, stir 30-60 minute, ageing 0.5-2 days; The precursor solution obtained;
The weight ratio of four hydration cobalt acetates, surfactant, hexamethylenetetramine, water-alcohol solvent, alcoholic solvent is 1:(1-5): (0.1-1): (50-150): (50-150);
In water-alcohol solvent, the volume ratio 1:(10-15 of water and alcohol);
B) precursor solution that ageing is good is transferred in reactor, at 100-200 DEG C, react 1-5h, centrifuge washing 3-6 time, clean solvent heat product is reacted 1-5h at 150-400 DEG C, be cooled to room temperature, be dried to constant weight, namely obtain cobaltosic oxide two-dimensional nano sheet (Co 3o 4-NSs);
C) X-factor solution is added Co 3o 4in-NSs dispersion liquid, stirred at ambient temperature 10-20h, uses ethanol and deionized water centrifuge washing 3 times successively, is dried to constant weight.
Co 3o 4-NSs dispersion liquid is by Co 3o 4-NSs is dissolved in water, and disperses 10-30 minute with ultrasonic wave; Co 3o 4-NSs is 1:100-1000 with the weight ratio of water;
X-factor and Co 3o 4the weight ratio of-NSs is 1:(1-5).
Described X-factor solution is for be dissolved in sodium hydroxide solution by X-factor, and the weight ratio of X-factor, NaOH, water is 1:1-10:1500-25000.
Described surfactant is polyethylene glycol grafting polypropylene glycol.
The alcohol of described water-alcohol solvent be selected from methyl alcohol, ethanol, propyl alcohol and ethylene glycol one or more.
Described alcoholic solvent be selected from methyl alcohol, ethanol, propyl alcohol and ethylene glycol one or more.
Pass through technique scheme, first the present invention utilizes the method for surfactant-polyethylene glycol grafting polypropylene glycol (P123) self assembly in water alcohol mixed solvent, the cobaltosic oxide nano sheet layer material Co being curing agent synthesis two-dimensional structure for raw material and six methine four ammoniums with four hydration cobalt acetates 3o 4-NSs); Then by functionalization molecule-X-factor (Hemin) and cobaltosic oxide nano lamella (Co 3o 4-NSs) directly carry out mix and blend under normal temperature, by the effect of physical absorption, X-factor (Hemin) is fixed to cobaltosic oxide nano lamella (Co 3o 4-NSs) on, thus prepare Hemin/Co 3o 4-NSs two-dimensional nano composite, i.e. Mimetic Peroxidase.
Compared with prior art, the cost with Mimetic Peroxidase is low, catalytic activity is high and good stability, the feature that detection range is wide in the present invention.
Other features and advantages of the present invention are described in detail in detailed description of the invention part subsequently.
Accompanying drawing explanation
Accompanying drawing is used to provide further explanation of the present invention, and forms a part for description, is used from explanation the present invention, but is not construed as limiting the invention with detailed description of the invention one below.In the accompanying drawings:
Fig. 1 is the cobaltosic oxide nano sheet (Co in detection 1 3o 4-NSs) scanning electron microscope (SEM) photograph.
Fig. 2 is the cobaltosic oxide (Hemin/Co of the functionalization in detection 1 3o 4-NSs) scanning electron microscope (SEM) photograph of nano composite material.
Fig. 3 is the uv absorption spectra in detection 2,
1 is functionalization molecule (Hemin); 2 is the cobaltosic oxide (Hemin/Co of functionalization 3o 4-NSs) nano composite material; 3 is cobaltosic oxide nano sheet (Co 3o 4-NSs).
Fig. 4 is cyclic voltammetry scan figure in detection 3.
4 is the cobaltosic oxide (Hemin/Co of functionalization 3o 4-NSs) nano composite material modified electrode; 5 is cobaltosic oxide nano sheet (Co 3o 4-NSs) modified electrode; 6 is bare electrode.
Fig. 5 be in embodiment 4 analogue enztme to the uv absorption spectra of hydrogen peroxide.
7 for adding Hemin/Co 3o 4the system of-NSs nano composite material, 8 for adding the system of Hemin, and 9 for adding Co 3o 4the system of-NSs, 10 is the blank system not adding any catalyst.
In Fig. 6 embodiment 5, analogue enztme is to the response curve of different concentration of hydrogen peroxide.
Detailed description of the invention
Below the specific embodiment of the present invention is described in detail.Should be understood that, detailed description of the invention described herein, only for instruction and explanation of the present invention, is not restricted to the present invention.
Below will be described the present invention by embodiment.In following examples, scanning electron microscope diagram spectrum parameter is by field emission scanning electron microscope (S-4800, HIT Hitachi) record, ultraviolet spectra graph parameter is by UV-2450 type ultraviolet specrophotometer (Shimadzu, Shimadzu Corporation of Japan) record, electrochemical parameter is recorded by electrochemical workstation (CHI660C, Shanghai Chen Hua company).
Polyethylene glycol grafting polypropylene glycol (P123) is purchased from the commercially available product of Sigma.Aldrich (St.Louis, USA) company.
Four hydration cobalt acetates buy the commercially available product in Beijing lark prestige Science and Technology Ltd..
X-factor (Hemin) and hexamethylenetetramine buy the commercially available product in Shanghai Aladdin Reagent Company.
Embodiment 1
1) P123 of 0.2g is joined 13g ethanol and 1g deionized water for stirring 15min; Under the condition stirred, then add 0.125gCo (Ac) 24H 2o and 0.07g six methine four ammonium continues to stir 15min; Finally, add 13mL ethylene glycol and stir 30min again, the precursor solution obtained ageing 1 day.
2) precursor solution after ageing is transferred in 45mL reactor, at 170 DEG C, react 2h, centrifuge washing.The 2h that dewatered at 250 DEG C by clean solvent heat product obtains cobaltosic oxide two-dimensional nano sheet (Co 3o 4-NSs).
3) by obtained 3mgCo 3o 4-NSs is dispersed in 1mL deionized water, ultrasonic disperse 30 minutes.
4) getting 1mgHemin joins in 12.65mL NaOH (NaOH: water=1:1916) solution, obtained Hemin storing solution.
5) Hemin storing solution is dropwise joined step 3) in Co 3o 4in-NSs dispersion liquid, stirred at ambient temperature 12h.After reaction terminates, use ethanol and deionized water centrifuge washing 3 times successively, to remove not by the Hemin molecule adsorbed, can Hemin/Co be obtained 3o 4-NSs two-dimensional nano composite.
By ESEM (S-4800, HIT Hitachi) to the Co in embodiment 1 3o 4-NSs and Hemin/Co 3o 4-NSs nano composite material carries out morphology characterization, and characterization result is shown in Fig. 1 (Co 3o 4-NSs) and Fig. 2 (Hemin/Co 3o 4-NSs).As seen from the figure, cobaltosic oxide nano sheet (Co 3o 4-NSs) with Hemin compound before and after pattern do not change, the two is the material of two-dimensional nano lamellar structure.
By UV-2450 type ultraviolet specrophotometer (Shimadzu, Japanese Shimadzu Corporation) to the Co in embodiment 1 3o 4-NSs, Hemin storing solution and Hemin/Co 3o 4-NSs nano composite material carries out UV absorbance detection, detection the results are shown in Figure 3.Known by the ultraviolet characteristic absorption peak in comparison diagram 3, Hemin and Hemin/Co 3o 4all there is characteristic absorption peak at 390nm place in-NSs, and Co 3o 4not there is characteristic absorption peak in-NSs, can illustrate that Hemin is successfully fixed to cobaltosic oxide nano sheet (Co 3o 4-NSs) on.
By electrochemical workstation (CHI660C, Shanghai Chen Hua company) to the Co in embodiment 1 3o 4-NSs, Hemin/Co 3o 4-NSs nano composite material and bare electrode carry out cyclic voltammetry scan, and what record the results are shown in Figure 4.As shown in Figure 4, Hemin/Co is only had 3o 4just there is a pair redox peak in the modified electrode of-NSs, this is by Fe in Hemin molecule 3+/ Fe 2+between carry out the signal peak of single electron transmission generation.This just further demonstrates Hemin molecule and is successfully fixed to cobaltosic oxide nano sheet (Co 3o 4-NSs) on, namely composite is successfully prepared.
Embodiment 2
1) P123 of 0.3g is joined 15g ethanol and 1g deionized water for stirring 15min; Under the condition stirred, then add 0.25gCo (Ac) 24H 2o and 0.1g six methine four ammonium continues to stir 15min; Finally, add 15mL ethylene glycol and stir 40min again, the precursor solution obtained ageing 1.5 days.
2) precursor solution after ageing is transferred in 45mL reactor, at 150 DEG C, react 5h, centrifuge washing.The 1.5h that dewatered at 300 DEG C by clean solvent heat product obtains cobaltosic oxide two-dimensional nano sheet (Co 3o 4-NSs).
3) by obtained 1mgCo 3o 4-NSs is dispersed in 1mL deionized water, ultrasonic disperse.
4) getting 1mgHemin joins in 12.65mL NaOH (NaOH: water=1:1500) solution, obtained Hemin storing solution.
5) Hemin storing solution is dropwise joined step 3) in Co 3o 4in-NSs dispersion liquid, stirred at ambient temperature 12h.After reaction terminates, use ethanol and deionized water centrifuge washing 3 times successively, to remove not by the Hemin molecule adsorbed, can Hemin/Co be obtained 3o 4-NSs two-dimensional nano composite.
Embodiment 3
1) P123 of 0.2g is joined 17g ethanol and 1g deionized water for stirring 30min; Under the condition stirred, then add 0.125gCo (Ac) 24H 2o and 0.1g six methine four ammonium continues to stir 15min; Finally, add 16mL ethylene glycol and stir 30min again, the precursor solution obtained ageing 2 days.
2) precursor solution after ageing is transferred in 45mL reactor, at 200 DEG C, react 1h, centrifuge washing.The 4h that dewatered at 150 DEG C by clean solvent heat product obtains cobaltosic oxide two-dimensional nano sheet (Co 3o 4-NSs).
3) by obtained 5mgCo 3o 4-NSs is dispersed in 1mL deionized water, ultrasonic disperse.
4) getting 1mgHemin joins in 12.65mL NaOH (NaOH: water=1:2500) solution, obtained Hemin storing solution.
5) Hemin storing solution is dropwise joined step 3) in Co 3o 4in-NSs dispersion liquid, stirred at ambient temperature 12h.After reaction terminates, use ethanol and deionized water centrifuge washing 3 times successively, to remove not by the Hemin molecule adsorbed, can Hemin/Co be obtained 3o 4-NSs two-dimensional nano composite.
Embodiment 4
1) phosphoric acid (PBS) cushioning liquid of 2.1mL, 0.1M, pH=6.0 is placed in cuvette, then adds 0.4mL5mMTMB and 50 μ L0.5MH 2o 2, finally add 50 μ L1mg/mLHemin/Co 3o 4-NSs (embodiment 1 is made) carries out catalytic reaction as catalyst, and the reaction time is 6min, and the color of solution gradually becomes blue from colourless.
2) control experiment adds 50 μ L1mg/mLCo at identical conditions 3o 4-NSs or 50 μ L0.1mg/mLHemin carries out catalytic reaction.By UV-2450 type ultraviolet specrophotometer (Shimadzu, Japanese Shimadzu Corporation), UV absorption sign is carried out to above-mentioned catalytic reaction, sign the results are shown in Figure 5.In Fig. 5, curve a is for adding 50 μ LHemin/Co 3o 4the absorption curve of-NSs, b curve is the absorption curve containing 50 μ LHemin, and c curve is for adding 50 μ LCo 3o 4the absorption curve of-NSs, d curve is the absorption curve of blank (not adding any catalyst), does not occur absworption peak.
As shown in Figure 5, Hemin/Co 3o 4-NSs can not only detect qualitatively to hydrogen peroxide, and under the same conditions, compared to other two kinds of analogue enztmes, Hemin/Co 3o 4the catalytic activity of-NSs is maximum, and this gives the credit to Hemin and Co 3o 4the synergy of-NSs.
Embodiment 5
Phosphoric acid (PBS) cushioning liquid of 2.1mL, 0.1M, pH=6.0 is placed in cuvette, then adds the H of 0.4mL5mMTMB (tetramethyl benzidine) and variable concentrations 2o 2, add 50 μ L1mg/mLHemin/Co 3o 4-NSs (embodiment 1), as catalyst, quantitatively detects hydrogen peroxide by UV absorption.That detects the results are shown in Figure 6, and wherein illustration is the range of linearity being detected hydrogen oxide.The detection line that can obtain hydrogen peroxide from the result detected is 2 × 10 -6m, the range of linearity that can detect is 10-50000 μ Μ, and the range of linearity can up to 3 orders of magnitude.Compared with similar Mimetic Peroxidase, Hemin/Co 3o 4-NSs has the advantage that preparation cost is low, catalytic activity is high, detectability is low and the range of linearity is wide.

Claims (7)

1. a preparation method for analogue enztme, described preparation method comprises the following steps:
A) surfactant is joined in water-alcohol solvent, stir 15-60 minute; Add four hydration cobalt acetates and six methine four ammoniums continuation stirring 15-60 minute again; Add alcoholic solvent again, stir 30-60 minute, ageing 0.5-2 days; The precursor solution obtained;
The weight ratio of four hydration cobalt acetates, surfactant, hexamethylenetetramine, water-alcohol solvent, alcoholic solvent is 1:(1-5): (0.1-1): (50-150): (50-150);
B) precursor solution that ageing is good is transferred in reactor, at 100-200 DEG C, react 1-5h, centrifuge washing 3-6 time, clean solvent heat product is reacted 1-5h at 150-400 DEG C, be cooled to room temperature, be dried to constant weight, namely obtain cobaltosic oxide two-dimensional nano sheet (Co 3o 4-NSs);
C) X-factor solution is added Co 3o 4in-NSs dispersion liquid, stirred at ambient temperature 10-20h, uses ethanol and deionized water centrifuge washing 3 times successively, is dried to constant weight;
X-factor and Co 3o 4the weight ratio of-NSs is 1:(1-5).
2. the preparation method of a kind of analogue enztme according to claim 1, is characterized in that: in described water-alcohol solvent, the volume ratio 1:(10-15 of water and alcohol).
3. the preparation method of a kind of analogue enztme according to claim 1, is characterized in that: described Co 3o 4-NSs dispersion liquid is by Co 3o 4-NSs is dissolved in water, and disperses 10-30 minute with ultrasonic wave; Co 3o 4-NSs is 1:100-1000 with the weight ratio of water.
4. the preparation method of a kind of analogue enztme according to claim 1, it is characterized in that: described X-factor solution is for be dissolved in sodium hydroxide solution by X-factor, and the weight ratio of X-factor, NaOH, water is 1:1-10:1500-25000.
5. the preparation method of a kind of analogue enztme according to claim 1, is characterized in that: described surfactant is polyethylene glycol grafting polypropylene glycol.
6. the preparation method of a kind of analogue enztme according to claim 1, is characterized in that: the alcohol of described water-alcohol solvent be selected from methyl alcohol, ethanol, propyl alcohol and ethylene glycol one or more.
7. the preparation method of a kind of analogue enztme according to claim 1, is characterized in that: described alcoholic solvent be selected from methyl alcohol, ethanol, propyl alcohol and ethylene glycol one or more.
CN201510925105.2A 2015-12-11 2015-12-11 Preparation method of mimic enzyme Pending CN105413750A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110479241A (en) * 2019-08-02 2019-11-22 电子科技大学 Improve the active processing method of peroxidase and product of nano enzyme
CN115779971A (en) * 2022-09-20 2023-03-14 天津科技大学 Cascade nanoenzyme and preparation method and application thereof

Citations (2)

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Publication number Priority date Publication date Assignee Title
CN104014370A (en) * 2014-05-30 2014-09-03 南京理工大学 Peroxide mimic enzyme and preparation and applications thereof
CN104568934A (en) * 2015-01-05 2015-04-29 上海纳米技术及应用国家工程研究中心有限公司 Application of nanometer cobaltosic oxide used as peroxide enzyme mimic for measuring concentration of hydrogen peroxide

Patent Citations (2)

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Publication number Priority date Publication date Assignee Title
CN104014370A (en) * 2014-05-30 2014-09-03 南京理工大学 Peroxide mimic enzyme and preparation and applications thereof
CN104568934A (en) * 2015-01-05 2015-04-29 上海纳米技术及应用国家工程研究中心有限公司 Application of nanometer cobaltosic oxide used as peroxide enzyme mimic for measuring concentration of hydrogen peroxide

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Title
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110479241A (en) * 2019-08-02 2019-11-22 电子科技大学 Improve the active processing method of peroxidase and product of nano enzyme
CN110479241B (en) * 2019-08-02 2021-09-28 电子科技大学 Treatment method for improving peroxidase-like activity of nano-enzyme and product
CN115779971A (en) * 2022-09-20 2023-03-14 天津科技大学 Cascade nanoenzyme and preparation method and application thereof

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